U.S. Pat. No. 4,284,574 relates to the preparation of diglycidyl ethers of di-secondary alcohols wherein the di-secondary alcohols are prepared by either (A) reaction of a monoglycidyl ether with a dihydric phenol in the presence of a basic catalyst, such as a tertiary amine, a quaternary ammonium base, an alkali metal hydroxide or quaternary ammonium salt or alternatively (B) reaction between an alcohol and a diglycidyl ether of a dihydric phenol in the presence of a basic catalyst, such as a tertiary amine, a quaternary ammonium base, an alkali metal hydroxide, quaternary ammonium salt or a Lewis acid catalyst, such as boron trifluoride complex or stannic chloride. The di-secondary alcohols are then glycidylized to produce the glycidyl ether. The glycidyl ethers produced in accordance with process (A) exhibit viscosities in the range of about 900 to 1500 cps at 25.degree. C. and those in accordance with process (B) exhibit viscosities in the range of greater than 3,000 cps at 25.degree. C. Lower viscosities are desirable in order to decrease or eliminate the amount of reactive diluent needed and it offers advantages in formulations containing large amounts of fillers.
A study of the suitability of liquid state C-13 NMR for investigating the chemical structures and the reaction course of reaction of diglycidyl ether of bisphenol A with 1,4-butandiol in the presence of magnesium perchlorate and N,N-dimethylbenzylamine is disclosed in Polymer Bulletin, Vol. 22, pp. 221-226 (1989). Use of magnesium perchlorate is disadvantageous due to its explosive nature and lower catalytic reactivity.
U.S. Pat. No. 4,543,430 discloses a process for the preparation of addition products of epoxides and hydroxylated compounds using as a catalyst a salt of trifluoromethane sulfonic acid.
Applicants have found catalysts for the preparation of addition products of an epoxide and an alcohol which provide products with equivalent or lower viscosities which indicates greater selectivity than those produced in accordance with U.S. Pat. No. 4,543,430.
Accordingly, it is an object of the present invention to provide a process for the production of glycidyl ethers of di-secondary alcohols of low viscosity, high purity and low easily hydrolyzable chlorine content.
It is further object of the present invention to provide a process for the production of mono- and polyglycidyl ethers of primary alcohols or diols.
It is a further object of the present invention to provide a process which reduces or eliminates the explosive hazard associated with the use of magnesium perchlorate as a catalyst in the preparation of di-secondary alcohols and aliphatic glycidyl ethers.
Applicants have surprisingly found that glycidyl ethers of di-secondary alcohols of low viscosity, high purity and low easily hydrolyzable chlorine content are obtained with the process of the present invention.
Various other objects and advantages of this invention will become apparent from the following description thereof.